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Highlights in Organic Chemistry The Photo SN1 Reaction Via Phenyl Cation

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Formation of an aryl-carbon bond by a nucleophilic substitution is limited to activated substituted aromatics and strong nucleophiles (SN2Ar path) or to good electron donors (SRN1 process). Aryl SN1 reactions forming new Ar-C bonds have now emerged as a convenient alternative and can be easily accomplished by reaction of phenyl cations (in their triplet state) with various nucleophiles (olefins, (hetero)arenes). These cations, thermally almost unaccessible, can be generated by photocleavage both from electron-rich phenyl chlorides, fluorides, mesylates, triflates and phosphates and from benzenediazonium salts. Some of these Ar-C bond forming reactions can be considered photochemical alternatives to metal catalyzed cross coupling reactions.

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Keywords: aryl-oxygen bond; fragment heterolitically; nucleophiles; photochemical behaviour; triplet phenyl cations

Document Type: Research Article

Affiliations: Department of Organic Chemistry, The University, V. Taramelli 10, 27100 Pavia, Italy.

Publication date: 2006-04-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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